Osborne Vancleef

Elf Rogue



Level = 5
XP = 6500
Armor Class = 15
Hit Points = 35/35
Hit Dice = d8 (5)
Speed = 35 ft

Strength = 4 (-3)
Dexterity = 18 (4)
Constitution = 14 (2)
Intelligence = 11 (0)
Wisdom = 12 (1)
Charisma = 12 (1)


Proficiency Bonus = +3
Ability Checks = Acrobatics, Insight, Perception, Persuasion, Sleight of Hand, Stealth (x2)
Saving Throws = Dexterity, Intelligence
Armor = Light
Weapons = Simple weapons, hand crossbows, longswords, rapiers, shortswords, shortbows, longbows
Tools = Thieves’ tools (x2), disguise kit, forgery kit
Languages = Common, Elvish


Shortsword (2) (F, L) = 1d6 piercing, +7 attack bonus
Dagger (2) (F, L, T) = 1d4 piercing, +7 attack bonus


Advantage on saving throws against being charmed
Can’t be put to sleep by magic
Four hours of trance counts as long rest
Mask of the Wild (can attempt to hide even when only lightly obscured by elements)
False Identity (second identity complete with documentation, acquaintances, disguises // can forge documents seen before)

Class Features

Sneak Attack (Extra 3d6 damage if advantage on attack roll, must be finesse or ranged weapon)
Expertise (Double two skill proficiencies)
Thieves’ cant (Understands secret thieves language)
Cunning Action (Can take bonus action of Dash, Disengage, or Hide on each turn)
Roguish Archetype (Assassin)
Archetype Bonus Proficiencies (Disguise kit and poisoner’s kit)
Assassinate (Advantage on attack rolls against any creature that hasn’t taken a turn, any hit against surprised creature is a crit)
Alert feat (Adds 5 to initiative, can’t be surprised, other creatures don’t gain advantage against even when they are hidden)
Uncanny Dodge (Halves any damage done)


Shortsword (2)
Leather armor
Boots of the Winterlands
Dagger (2)
Thieves’ tools
Burglar’s Pack (backpack, 1000 ball bearings, 10 ft. of string, a bell, 5 candles, a crowbar, a hammer, 10 pitons, a hooded lantern, two flasks of oil, 5 days of rations, a tinderbox, a waterskin, 50 ft. hempen rope)
Disguise kit
Forgery kt
Weighted die
Trinket (a glass eye)


Basic Info

Age = 140
Height = 5’10"
Weight = 165
Eyes = Green
Skin = White
Hair = Black

Alignment = Chaotic Neutral
Background = Charlatan

Personality traits = Born gambler who can’t resist taking a risk for a potential payoff // I pocket anything that might have some value
Ideals = I never run the same con twice (Creativity)
Bonds = A powerful person killed someone I love. Someday soon, I’ll have my revenge.
Flaws = I’m convinced no one could ever fool me the way I fool others // I can’t resist swindling people who are more powerful than me


As a member of the Redbrand ruffians, Osborne Vancleef relished the feeling of being able to take anything he wanted through various deceptive means. His desire for great material wealth pushed him to develop a specific skill set centered around speed, stealth, and trickery. It wasn’t until his financial gluttony cost him dearly that he abandoned the Redbrands. The Redbrands now serve as a reminder of that fateful day when Osborne’s younger brother, a newly trained member of the group, was slain during a routine impersonation con. The target was underestimated and dealt a killing blow in reprisal for the attempted robbery. Osborne, having witnessed this tragic event, vowed revenge. Whether he had to swindle, deceive, or fight, Osborne Vancleef knew his quest for vengeance wouldn’t be stopped until he stood above the lifeless body of his greatest foe.

Osborne Vancleef

A Series of Unfortunate Rolls dmonroy911